WO2021255047A1 - Hair conditioning composition for improved deposition - Google Patents

Hair conditioning composition for improved deposition Download PDF

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Publication number
WO2021255047A1
WO2021255047A1 PCT/EP2021/066150 EP2021066150W WO2021255047A1 WO 2021255047 A1 WO2021255047 A1 WO 2021255047A1 EP 2021066150 W EP2021066150 W EP 2021066150W WO 2021255047 A1 WO2021255047 A1 WO 2021255047A1
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WIPO (PCT)
Prior art keywords
conditioning
atom
composition
chain length
carbon
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PCT/EP2021/066150
Other languages
French (fr)
Inventor
Richard Jonathan BARFOOT
Michael James Cooke
Cesar Ernesto MENDOZA FERNANDEZ
Paul Damien Price
Original Assignee
Unilever Ip Holdings B.V.
Unilever Global Ip Limited
Conopco, Inc., D/B/A Unilever
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Application filed by Unilever Ip Holdings B.V., Unilever Global Ip Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever Ip Holdings B.V.
Priority to EP21731817.9A priority Critical patent/EP4167924A1/en
Priority to US18/011,109 priority patent/US20230255867A1/en
Priority to MX2022016145A priority patent/MX2022016145A/en
Priority to JP2022577350A priority patent/JP2023537188A/en
Priority to BR112022023902A priority patent/BR112022023902A2/en
Priority to CN202180043508.8A priority patent/CN115942928A/en
Publication of WO2021255047A1 publication Critical patent/WO2021255047A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/042Gels
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds

Definitions

  • the invention is concerned with conditioning compositions for the treatment of hair, containing a combination of primary and secondary surfactants having linear alkyl groups of different chain length comprising at least one amido group, and a benefit agent to be deposited onto the hair during use and particularly relates to a conditioning composition that enables increased amounts of benefit agent to be deposited.
  • compositions such as hair treatment compositions
  • benefit agents are often key drivers of product performance.
  • many of the hair conditioner products in the market today work to deliver benefits to hair by depositing benefit agents such as fragrance materials, silicones and damage repair actives onto the hair during the wash and care process.
  • compositions that provide improved delivery of benefit materials to a surface, for example hair.
  • Various types of cationic compounds are known in hair treatment compositions for a variety of benefits.
  • WO 17/172117 discloses a composition for treating keratinous substrates comprising a cationic agent comprising a defined first quaternary ammonium compound and an imidazoline compound, a modified starch, two silane compounds, a cationic vinylpyrrolidone polymer and water. Hair treated with the compositions is purported to have improved mass, body, volume, to be easily rinsed, to dry fast, to stay clean longer and be sufficiently conditioned.
  • US 2005/175569 discloses cosmetic compositions, for example for conditioning and styling hair, comprising a cationic surfactant, which may be a quaternary ammonium salt.
  • JP 2005-060271 discloses an aqueous hair cosmetic composition that can comprise (A) a dimethylpolysiloxane represented by general formula (1), (B) a dimethylpolysiloxane represented by general formula (2), (C) a cyclic dimethylpolysiloxane represented by general formula (3) at a ratio of [(B)+(C)]/(A) greater than or equal to 1; and (D) an additional quaternary ammonium component.
  • the composition is said to provide a range of conditioning benefits to hair in the wet, rinse and dry stages.
  • compositions comprising a combination of cationic conditioning primary surfactants with cationic co-surfactants, each having a linear alkyl chain of defined length, and used at a specific ratio, providean unexpectedly large enhancement in the deposition of benefit agents whilst maintaining excellent product rheology, particularly viscosity and yield stress.
  • a conditioning composition comprising:
  • Ri comprises a linear alkyl chain having a carbon-carbon chain length of from Cie to C24, preferably C18 to C22;
  • R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C 4 , preferably Ci to C 2 or a benzyl group;
  • X is an organic or inorganic anion
  • R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2or a benzyl group;
  • R3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 10 to 14;
  • X is an organic or inorganic anion; wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R 3 in structure 2 by at least 3 atoms, such that the atom-atom chain length of Ri in structure 1 is longer than the atom-atom chain length of R 3 in structure 2; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1 :20 to 1 :1.
  • the invention provides a method of increasing deposition of a particulate benefit agent selected from conditioning actives, preferably silicone emulsion and mixtures thereof to hair comprising the step of applying to hair a conditioning composition of the first aspect.
  • a particulate benefit agent selected from conditioning actives, preferably silicone emulsion and mixtures thereof to hair comprising the step of applying to hair a conditioning composition of the first aspect.
  • the method of the invention preferably comprises an additional step of rinsing the composition from the hair.
  • the method is a method of increasing silicone deposition to hair comprising the steps of applying to hair a composition as defined by the first aspect of the invention comprising silicone emulsion and rinsing the hair with water.
  • compositions in accordance with the invention are preferably formulated as conditioners for the treatment of hair (typically after shampooing) and subsequent rinsing.
  • the conditioning compositions of the invention are not cleansing compositions and, as such, do not comprise anionic cleansing surfactants, for example sodium lauryl ether sulphate.
  • the treatment composition is selected from a rinse-off hair conditioner, a hair mask, a leave-on conditioner composition, and a pre-treatment composition, more preferably selected from a rinse-off hair conditioner, a hair mask, a leave-on conditioner composition, and a pre-treatment composition, for example an oil treatment, and most preferably selected from a rinse-off hair conditioner, a hair mask and a leave-on conditioner composition.
  • the treatment composition is preferably selected from a rinse-off hair conditioner and a leave-on conditioner.
  • Rinse off conditioners for use in the invention are conditioners that are typically left on wet hair for 1 to 2 minutes before being rinsed off.
  • Hair masks for use in the present invention are treatments that are typically left on the hair for 3 to 10 minutes, preferably from 3 to 5 minutes, more preferably 4 to 5 minutes, before being rinsed off.
  • Leave-on conditioners for use in the invention are typically applied to the hair and left on the hair for more than 10 minutes, and preferably are applied to the hair after washing and not rinsed out until the next wash.
  • compositions of the invention comprise 0.01 to 10 wt % of a linear cationic conditioning primary surfactant; selected from structure 1 and mixtures thereof
  • Ri comprises a linear alkyl chain having a carbon-carbon chain length of from Cie to C24, preferably C18 to C22;
  • R 2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C 4 , preferably Ci to C 2 or a benzyl group;
  • X is an organic or inorganic anion.
  • the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R 3 in structure 2 by from 3 to 12, more preferably from 4 to 12, even more preferably from 6 to 12, most preferably from 6 to 10 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R 3 in structure 2.
  • the amine head group is charged within the final formulation.
  • Raw materials include, however, species where the charge is not permanent and can be induced by protonation in the formulation using a strong acid.
  • R2 is a proton in the above general formulae therefore, the proton may be present in the raw material or become associated during formulation.
  • the alkyl groups may comprise one or more ester (-OCO- or -COO-), amido (- NOC- or NCO-), and/or ether (-0-) linkages within the alkyl chain.
  • Alkyl groups may optionally be substituted with one or more hydroxyl groups.
  • Alkyl groups may be straight chain or branched and, for alkyl groups having 3 or more carbon atoms, cyclic.
  • the alkyl groups may be saturated or may contain one or more carbon-carbon double bonds (e.g., oleyl).
  • Alkyl groups are optionally ethoxylated on the alkyl chain with one or more ethyleneoxy groups.
  • Suitable quaternary amine salts for use in conditioner compositions according to the invention are quaternary amine salt comprising from 12 to 24 carbon atoms, preferably from 16 to 22 carbon atoms.
  • Suitable quaternary amine salts for use in conditioner compositions according to the invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, Behentrimonium methosulphate, BehenylAmido Propyl Di-Methyl Amine, cetyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, Stearalkonium Chloride, Stearalkonium methosulphate, didodecyldimethylammonium chloride, dioctade
  • Preferred quaternary amine salts selected from behenyltrimethylammonium chloride, Behentrimonium methosulphate, cetyltrimethylammonium chloride, and mixtures thereof.
  • a particularly useful cationic surfactant for use in conditioners according to the invention is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex Hoechst Celanese.
  • Another particularly preferred cationic surfactant for use in conditioners according to the invention is behenyltrimethylammonium chloride, available commercially, for example as GENAMIN KDMP, ex Clariant.
  • Suitable cationic surfactants include those materials having the CTFA designations Quaternium-5, Quaternium-31, and Quaternium-18. Mixtures of any of the foregoing materials may also be suitable.
  • Suitable cationic surfactants for use in the invention is a combination of (i) and (ii) below:
  • R 1 CONH(CH 2 ) m N(R 2 )R 3 (ll) in which R 1 is a hydrocarbyl chain having 10 or more carbon atoms, R 2 and R 3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and m is an integer from 1 to about 10; and
  • hydrocarbyl chain means an alkyl or alkenyl chain.
  • Preferred amidoamine compounds are those corresponding to formula (I) in which
  • R 1 is a hydrocarbyl residue having from about 11 to about 24 carbon atoms
  • R 2 and R 3 are each independently hydrocarbyl residues, preferably alkyl groups, having from 1 to about 4 carbon atoms, and m is an integer from 1 to about 4.
  • R 2 and R 3 are methyl or ethyl groups.
  • m is 2 or 3, i.e. an ethylene or propylene group.
  • Preferred amidoamines useful herein include stearamido-propyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyl- diethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethyl-amine, behenamidopropyldiethylmine, behenamidoethyldiethyl-amine, behenamidoethyldimethylamine, arachidamidopropyl- dimethylamine, arachidamidopropyldiethylamine, arachid-amidoethyldiethylamine, arachida
  • amidoamines useful herein are stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.
  • amidoamines useful herein include: stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan), stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikko, behenamidopropyldimethylamine with a tradename INCROMINE BB available from Croda (North Humberside, England), and various amidoamines with tradenames SCHERCODINE series available from Scher (Clifton New Jersey, USA).
  • Acid may be any organic or mineral acid which is capable of protonating the amidoamine in the conditioner composition.
  • Suitable acids useful herein include hydrochloric acid, acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof.
  • the acid is selected from the group consisting of acetic acid, tartaric acid, hydrochloric acid, fumaric acid, lactic acid and mixtures thereof.
  • the primary role of the acid is to protonate the amidoamine in the hair treatment composition thus forming a tertiary amine salt (TAS) in situ in the hair treatment composition.
  • TAS tertiary amine salt
  • the TAS in effect is a non-permanent quaternary ammonium or pseudo quaternary ammonium cationic surfactant.
  • the acid is included in a sufficient amount to protonate more than 95 mole% (293 K) of the amidoamine present.
  • the level of linear cationic conditioning primary surfactant will generally range from 0.01 to 10%, more preferably 0.05 to 7.5%, most preferably 0.1 to 5% by total weight of the composition.
  • composition of the invention comprises from 0.1 to 10 wt % of a linear fatty material.
  • fatty materials and cationic surfactants in conditioning compositions is believed to be especially advantageous, because this leads to the formation of a structured lamellar or liquid crystal phase, in which the cationic surfactant is dispersed.
  • fatty material is meant a fatty alcohol, an alkoxylated fatty alcohol, a fatty acid or a mixture thereof.
  • the linear fatty material is selected from a fatty alcohol and a fatty acid, most preferably a fatty alcohol.
  • the alkyl chain of the fatty material is fully saturated.
  • Representative fatty materials comprise from 8 to 22 carbon atoms, more preferably 16 to 22.
  • Suitable fatty alcohols comprise from 8 to 22 carbon atoms, preferably 16 to 22, most preferably C16 to C18.
  • Fatty alcohols are typically compounds containing straight chain alkyl groups. Preferably, the alkyl groups are saturated. Examples of preferred fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof. The use of these materials is also advantageous in that they contribute to the overall conditioning properties of compositions for use in the invention.
  • Alkoxylated, (e.g. ethoxylated or propoxylated) fatty alcohols having from about 12 to about 18 carbon atoms in the alkyl chain can be used in place of, or in addition to, the fatty alcohols themselves. Suitable examples include ethylene glycol cetyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (4) cetyl ether, and mixtures thereof.
  • the level of fatty material in conditioners of the invention is suitably from 0.01 to 10, preferably from 0.1 to 10, and more preferably from 0.1 to 5 percent by weight of the total composition.
  • the weight ratio of cationic surfactant to fatty alcohol is suitably from 10:1 to 1 :10, preferably from 4:1 to 1 :8, optimally from 1:1 to 1 :7, for example 1:3.
  • composition of the invention comprises a particulate benefit agent.
  • the particulate benefit agent is selected from conditioning actives, and mixtures thereof.
  • the particulate benefit agent is a conditioning active selected from silicone emulsions, oils and mixtures thereof, most preferably silicone emulsions. More preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, hydrocarbon oils, fatty esters and mixtures thereof, most preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, polyisobutylene, cocoa butter, palm stearin, sunflower oil, soyabean oil, coconut oil and mixtures thereof.
  • silicones and oils are present in emulsified form in compositions of the invention.
  • Suitable oils are selected from hydrocarbon oils, fatty esters and mixtures thereof.
  • Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are branched chain hydrocarbon oils will preferably contain from about 12 to about 42 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers.
  • hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof.
  • Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used.
  • Another suitable material is polyisobutylene.
  • Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols, Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
  • Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically the mono-, di-, and tri-esters of glycerol and long chain carboxylic acids such as C1-C22 carboxylic acids.
  • Preferred materials include cocoa butter, palm stearin, sunflower oil, soyabean oil and coconut oil.
  • Preferred silicones are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, more preferably selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of aminofunctionalised silicones with dimethicones.
  • the particulate benefit agent is a conditioning active selected from silicone emulsions, oils and mixtures thereof, most preferably silicone emulsions. More preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, hydrocarbon oils, fatty esters and mixtures thereof, most preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, polyisobutylene, cocoa butter, palm stearin, sunflower oil, soyabean oil, coconut oil and mixtures thereof.
  • silicones and oils are present in emulsified form in compositions of the invention.
  • Suitable oils are selected from hydrocarbon oils, fatty esters and mixtures thereof.
  • Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are branched chain hydrocarbon oils will preferably contain from about 12 to about 42 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers.
  • hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof.
  • Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used.
  • Another suitable material is polyisobutylene.
  • Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols, Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
  • Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically the mono-, di-, and tri-esters of glycerol and long chain carboxylic acids such as C1-C22 carboxylic acids.
  • Preferred materials include cocoa butter, palm stearin, sunflower oil, soyabean oil and coconut oil.
  • Preferred silicones are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, more preferably selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of aminofunctionalised silicones with dimethicones.
  • silicone emulsions do not comprise a hydrophobic modification, preferably the silicone emulsion is not a myristyloxyl modified silicone, most preferably not a myristyloxyl modified silicone or a cetyloxyl modified silicone.
  • the silicone emulsions for use in the compositions of the invention are selected from emulsions of dimethicone, dimethiconol, amodimethicone and mixtures thereof.
  • Suitable silicones include polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable for use compositions of the invention are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Preferably, the silicone is selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of amino- functionalised silicones with dimethicones.
  • the viscosity of the emulsified silicone itself (not the emulsion or the final hair conditioning composition) is typically at least 10,000 cst at 25 °C the viscosity of the silicone itself is preferably at least 60,000 cst, most preferably at least 500,000 cst, ideally at least 1 ,000,000 cst. Preferably the viscosity does not exceed 10 9 cst for ease of formulation.
  • Emulsified silicones for use in the compositions of the invention will typically have a D90 silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 micron, ideally from 0.01 to 1 micron. Silicone emulsions having an average silicone droplet size (D50) of 0.15 micron are generally termed microemulsions.
  • Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.
  • Suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions /microemulsions of dimethiconol. Cross-linked silicone gums are also available in a pre emulsified form, which is advantageous for ease of formulation.
  • a further preferred class of silicones for inclusion in compositions of the invention are amino functional silicones.
  • amino functional silicone is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group.
  • suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone”.
  • a preferred amodimethicone is commercially available from Dow Corning as DC 7134.
  • amino functional silicones suitable for use in the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning).
  • Suitable quaternary silicone polymers are described in EP-A-0530 974.
  • a preferred quaternary silicone polymer is K3474, ex Goldschmidt.
  • Also suitable are emulsions of amino functional silicone oils with non ionic and/or cationic surfactant.
  • Pre-formed emulsions of amino functional silicone are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2-7224, DC2-8467, DC2-8177 and DC2-8154 (all ex Dow Corning).
  • Preferred conditioning actives are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, blends of aminofunctionalised silicones with dimethicones, hydrocarbon oils, fatty esters and mixtures thereof.
  • the total amount of particulate benefit agent conditioning active is preferably from 0.1 wt % to 10 wt % of the total composition more preferably from 0.1 wt % to 5 wt %, most preferably 0.25 wt % to 3 wt % is a suitable level.
  • composition of the invention comprises a linear cationic co-surfactant, according to structure 2: Structure 2 wherein:
  • R 2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C 4 , preferably Ci to C 2 or a benzyl group;
  • R 3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 10 to 14;
  • X is an organic or inorganic anion; wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R 3 in structure 2 by at least 3 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R 3 in structure 2; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1:20 to 1:1 , preferably from 1:10 to 1 :1 , preferably 1:5 to 1 :2.
  • the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R 3 in structure 2 by from 3 to 12, more preferably from 4 to 12, even more preferably from 6 to 12, most preferably from 6 to 10 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R 3 in structure 2.
  • R 3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 3 to 14, more preferably 6 to 14, even more preferably 8 to 14, most preferably 10 to 14 .
  • the linear co-surfactant is present in an amount of from 0.01 to 5 wt %, preferably 0.1 to 2, more preferably 0.1 to 1.0, most preferably 0.2 to 0.7 wt % based on weight of total composition)
  • X is an organic or inorganic anion.
  • X comprises an anion selected from the halide ions; sulphates of the general formula RSO 3 , wherein R is a saturated or unsaturated alkyl radical having 1 to 4 carbon atoms, and anionic radicals of organic acids.
  • Preferred halide ions are selected from fluoride, chloride, bromide and iodide.
  • Preferred anionic radicals of organic acids are selected from maleate, fumarate, oxalate, tartrate, citrate, lactate and acetate.
  • Preferred sulphates are methanesulphonate and ethanesulphonate.
  • X- comprises an anion selected from a halide, a methanesulfonate group and an ethanesulphonate group.
  • R3 comprises linear alkyl chains, saturated or unsaturated, comprising an amido group and with atom-atom chain lengths of from 10 to 14;
  • R2 comprises a proton or an alkyl chain having a carbon-carbon chain length of from Ci to C2;
  • X is selected from a halide, methanesulphonate and ethanesulphonate.
  • An example of a suitable material according to structure 2 is caprylamidopropyl dimethylamine, available from Sigma Aldrich.
  • composition rheology Composition rheology
  • compositions of the invention provide good viscosity and yield stress properties.
  • compositions have a preferred yield stress range of from 30 to 200 Pascals (Pa), most preferably from 40 to 150 Pa peak value at 25 °C and 1 Hz.
  • the method to measure the yield stress uses a serrated parallel-plate geometry, 40mm in diameter, attached to a suitable rheometer capable of applying oscillations at a constant frequency of 1Hz, and an amplitude sweep in the range of 0.1% to 2000%.
  • the amplitude sweep range is applied at no more than ten points per decade of strain range covered at no more than 4 cycles per amplitude.
  • the instrument should be operated under controlled strain, such as with the ARES G2 Rheometer from TA Instruments.
  • the geometry’s temperature should be set at 25°C by means of, for example, a Peltier-controlled plate, or a recirculating bath.
  • the yield stress is determined by plotting the elastic stress against strain amplitude, and at the peak of the curve, the maximum value is quoted as the yield stress.
  • the elastic stress is calculated as the multiplication of (storage modulus)*(strain amplitude), each readily obtained from the instrument.
  • compositions preferably have a viscosity of from 5,000 to 750,000 centipoise, preferably from 50,000 to 600,000 centipoise, more preferably from 50,000 to 450,000 as measured at 30°C on a Brookfield RVT using a Spindle A or B at 0.5 rpm for 60 seconds on a Helipath stand.
  • a preferred conditioner comprises a conditioning gel phase. These conditioners have little or no vesicle content. Such conditioners and methods for making them are described in WO2014/016354, WO2014/016353, WO2012/016352 and WO2014/016351.
  • a composition comprising such a conditioning gel phase confers a Draw Mass of from 1 to 250 g, preferably 2 to 100 g, more preferably 2 to 50 g, even more preferably 5 to 40 g and most preferably 5 to 25 g to hair treated with the composition.
  • Draw Mass is the mass required to draw a hair switch through a comb or brush.
  • the more tangled the hair the greater the mass required to pull the switch through the comb or brush, and the greater the level of condition of the hair, the lower the Draw Mass.
  • the Draw Mass is the mass required to draw a hair switch, for example of weight 1 to 20 g, length 10 to 30 cm, and width 0.5 to 5 cm through a comb or brush, as measured by first placing the hair switch onto the comb or brush, such that from 5 to 20 cm of hair is left hanging at the glued end of the switch, and then adding weights to the hanging end until the switch falls through the comb or brush.
  • the hair switch is of weight 1 to 20 g, more preferably 2 to 15 g, most preferably from 5 to10 g.
  • the hair switch has a length of from 10 to 40 cm, more preferably from 10 to 30 cm, and a width of from 0.5 to 5 cm, more preferably from 1.5 to 4 cm.
  • the Draw Mass is the mass required to draw a hair switch, for example of weight 10 g, length 20 cm, and width 3 cm through a comb or brush, as measured by first placing the hair switch onto the comb or brush, such that from 20 cm of hair is left hanging at the glued end of the switch, and then adding weights to the hanging end until the switch falls through the comb or brush.
  • composition according to the invention may comprise any of a number of ingredients which are common to hair conditioning compositions.
  • ingredients may include, preservatives, colouring agents, polyols such as glycerine and polypropylene glycol, chelating agents such as EDTA, antioxidants such as vitamin E acetate, fragrances, antimicrobials and sunscreens.
  • chelating agents such as EDTA
  • antioxidants such as vitamin E
  • ingredients are included individually at a level of up to 2%, preferably up to 1 %, by weight of the total composition.
  • compositions of the invention are preferably free from thickening agents for example thickening polymers.
  • thickening polymers include polyquaternium thickeners (such as polyquaternium-10, polyquaternium-39); guar based thickeners (such as guar hydroxy ammonium chloride); Polyethylene Glycol (PEG) based thickeners (such as PEG 90M, PEG 14M, PEG 150 distearate), etc.
  • Example 1 Composition 1 in accordance with the invention and Comparative
  • composition A Composition A
  • Example 1 Compositions of Example 1 in accordance with the invention and a comparative Example A. Amounts are shown in wt % by wt of total composition.
  • the conditioners in examples 1 and A can be prepared using the following method:
  • Surfactants and fatty materials are added to a suitable vessel and heated to above the melting point of the fatty materials.
  • the molten blend is added to a suitable amount of water according to the compositions in Table 1, at a temperature of between room temperature and below the melting point of the fatty materials.

Abstract

A conditioning composition provides superior deposition of benefit agent to hair, said composition comprising: • (i) 0.01 to 10 wt % of a linear cationic conditioning primary surfactant; selected from structure 1 and mixtures thereof: (ii) 0.1 to 10 wt % of a linear fatty material; • (iii) a particulate benefit agent selected from conditioning actives and mixtures thereof; • (iv) 0.01 to 5 wt %,, of a linear cationic co-surfactant, selected from structure 2 and mixtures thereof; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1:20 to 1:1.

Description

HAIR CONDITIONING COMPOSITION FOR IMPROVED DEPOSITION
Field of the Invention
The invention is concerned with conditioning compositions for the treatment of hair, containing a combination of primary and secondary surfactants having linear alkyl groups of different chain length comprising at least one amido group, and a benefit agent to be deposited onto the hair during use and particularly relates to a conditioning composition that enables increased amounts of benefit agent to be deposited.
Background and Prior art
In personal care compositions, such as hair treatment compositions, the deposition and delivery of benefit agents are often key drivers of product performance. For example, many of the hair conditioner products in the market today work to deliver benefits to hair by depositing benefit agents such as fragrance materials, silicones and damage repair actives onto the hair during the wash and care process.
However, consumers report being disappointed by the level of benefit derived from use of some compositions. This is usually caused by insufficient amount of benefit agents being delivered to the surface. It is, therefore, desirable to develop compositions that provide improved delivery of benefit materials to a surface, for example hair.
Various types of cationic compounds are known in hair treatment compositions for a variety of benefits.
WO 17/172117 discloses a composition for treating keratinous substrates comprising a cationic agent comprising a defined first quaternary ammonium compound and an imidazoline compound, a modified starch, two silane compounds, a cationic vinylpyrrolidone polymer and water. Hair treated with the compositions is purported to have improved mass, body, volume, to be easily rinsed, to dry fast, to stay clean longer and be sufficiently conditioned. US 2005/175569 discloses cosmetic compositions, for example for conditioning and styling hair, comprising a cationic surfactant, which may be a quaternary ammonium salt. JP 2005-060271 discloses an aqueous hair cosmetic composition that can comprise (A) a dimethylpolysiloxane represented by general formula (1), (B) a dimethylpolysiloxane represented by general formula (2), (C) a cyclic dimethylpolysiloxane represented by general formula (3) at a ratio of [(B)+(C)]/(A) greater than or equal to 1; and (D) an additional quaternary ammonium component. The composition is said to provide a range of conditioning benefits to hair in the wet, rinse and dry stages.
Our own published applications WO 02/102334 and WO 01/43718 provide aqueous hair treatment compositions having cleansing and conditioning properties that comprise quaternary ammonium based cationic surfactants having defined hydrocarbyl chains.
Whilst cationic materials are known in home and personal care products, there is a persistent need to provide improved deposition of benefit agents onto hair.
Despite the prior art, there remains a need to deliver improved delivery of benefits to hair without compromising on consumer desired viscosity characteristics. Consumers strongly prefer thicker products as they associate this with efficacy and quality. However, if it is too thick, pouring from a bottle can become difficult.
Experienced formulators in the field normally compensate for reduced viscosity by adding viscosity modifiers such as polymeric thickeners. However, this brings on other problems such as processing complications, lumpy appearance (the so-called “fish eye” appearance) as well as environmental and cost impact.
We have now surprisingly found that compositions comprising a combination of cationic conditioning primary surfactants with cationic co-surfactants, each having a linear alkyl chain of defined length, and used at a specific ratio, providean unexpectedly large enhancement in the deposition of benefit agents whilst maintaining excellent product rheology, particularly viscosity and yield stress.
All percentages quoted herein are by weight based on total weight, unless otherwise stated. All amounts quoted herein are based on 100 % activity of materials, unless otherwise stated. Definition of the Invention
Accordingly, there is provided a conditioning composition comprising:
(i) 0.01 to 10 wt % of a linear cationic conditioning primary surfactant; selected from structure 1 and mixtures thereof:
R2 R
R N Q _2 X
1 © F¾
Structure 1 wherein:
• Ri comprises a linear alkyl chain having a carbon-carbon chain length of from Cie to C24, preferably C18 to C22;
• R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2 or a benzyl group; and
• X is an organic or inorganic anion;
(ii) 0.1 to 10 wt % of a linear fatty material;
(iii) a particulate benefit agent selected from conditioning actives and mixtures thereof; and
(iv) 0.01 to 5 wt % of a linear cationic co-surfactant, selected from structure 2 and mixtures thereof
Figure imgf000004_0001
Structure 2 wherein:
• R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2or a benzyl group;
• R3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 10 to 14; and
• X is an organic or inorganic anion; wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R3 in structure 2 by at least 3 atoms, such that the atom-atom chain length of Ri in structure 1 is longer than the atom-atom chain length of R3 in structure 2; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1 :20 to 1 :1.
In a second aspect, the invention provides a method of increasing deposition of a particulate benefit agent selected from conditioning actives, preferably silicone emulsion and mixtures thereof to hair comprising the step of applying to hair a conditioning composition of the first aspect.
The method of the invention preferably comprises an additional step of rinsing the composition from the hair.
Preferably, the method is a method of increasing silicone deposition to hair comprising the steps of applying to hair a composition as defined by the first aspect of the invention comprising silicone emulsion and rinsing the hair with water.
Compositions in accordance with the invention are preferably formulated as conditioners for the treatment of hair (typically after shampooing) and subsequent rinsing.
The conditioning compositions of the invention are not cleansing compositions and, as such, do not comprise anionic cleansing surfactants, for example sodium lauryl ether sulphate.
General description of the invention
Preferably, the treatment composition is selected from a rinse-off hair conditioner, a hair mask, a leave-on conditioner composition, and a pre-treatment composition, more preferably selected from a rinse-off hair conditioner, a hair mask, a leave-on conditioner composition, and a pre-treatment composition, for example an oil treatment, and most preferably selected from a rinse-off hair conditioner, a hair mask and a leave-on conditioner composition. The treatment composition is preferably selected from a rinse-off hair conditioner and a leave-on conditioner. Rinse off conditioners for use in the invention are conditioners that are typically left on wet hair for 1 to 2 minutes before being rinsed off.
Hair masks for use in the present invention are treatments that are typically left on the hair for 3 to 10 minutes, preferably from 3 to 5 minutes, more preferably 4 to 5 minutes, before being rinsed off.
Leave-on conditioners for use in the invention are typically applied to the hair and left on the hair for more than 10 minutes, and preferably are applied to the hair after washing and not rinsed out until the next wash.
The linear cationic conditioning primary surfactant (i)
Compositions of the invention comprise 0.01 to 10 wt % of a linear cationic conditioning primary surfactant; selected from structure 1 and mixtures thereof
¾R
N Q _
R 2 X
1 © F¾
Structure 1 wherein:
• Ri comprises a linear alkyl chain having a carbon-carbon chain length of from Cie to C24, preferably C18 to C22;
• R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2 or a benzyl group; and
• X is an organic or inorganic anion.
Preferably, the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R3 in structure 2 by from 3 to 12, more preferably from 4 to 12, even more preferably from 6 to 12, most preferably from 6 to 10 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R3 in structure 2.
In structure 1, the amine head group is charged within the final formulation. Raw materials include, however, species where the charge is not permanent and can be induced by protonation in the formulation using a strong acid. When R2 is a proton in the above general formulae therefore, the proton may be present in the raw material or become associated during formulation.
Optionally, the alkyl groups may comprise one or more ester (-OCO- or -COO-), amido (- NOC- or NCO-), and/or ether (-0-) linkages within the alkyl chain. Alkyl groups may optionally be substituted with one or more hydroxyl groups. Alkyl groups may be straight chain or branched and, for alkyl groups having 3 or more carbon atoms, cyclic. The alkyl groups may be saturated or may contain one or more carbon-carbon double bonds (e.g., oleyl). Alkyl groups are optionally ethoxylated on the alkyl chain with one or more ethyleneoxy groups.
Suitable quaternary amine salts for use in conditioner compositions according to the invention are quaternary amine salt comprising from 12 to 24 carbon atoms, preferably from 16 to 22 carbon atoms.
Suitable quaternary amine salts for use in conditioner compositions according to the invention include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, Behentrimonium methosulphate, BehenylAmido Propyl Di-Methyl Amine, cetyltrimethylammonium chloride, cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, Stearalkonium Chloride, Stearalkonium methosulphate, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride dihydrogenated tallow dimethyl ammonium chloride (e.g., Arquad 2HT/75 from Akzo Nobel) and cocotrimethylammonium chloride.
Preferred quaternary amine salts selected from behenyltrimethylammonium chloride, Behentrimonium methosulphate, cetyltrimethylammonium chloride, and mixtures thereof.
A particularly useful cationic surfactant for use in conditioners according to the invention is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, ex Hoechst Celanese. Another particularly preferred cationic surfactant for use in conditioners according to the invention is behenyltrimethylammonium chloride, available commercially, for example as GENAMIN KDMP, ex Clariant.
Further suitable cationic surfactants include those materials having the CTFA designations Quaternium-5, Quaternium-31, and Quaternium-18. Mixtures of any of the foregoing materials may also be suitable.
Another example of a class of suitable cationic surfactants for use in the invention, either alone or together with one or more other cationic surfactants, is a combination of (i) and (ii) below:
(i) an amidoamine corresponding to the general formula (II):
R1CONH(CH2)mN(R2)R3(ll) in which R1 is a hydrocarbyl chain having 10 or more carbon atoms, R2 and R3 are independently selected from hydrocarbyl chains of from 1 to 10 carbon atoms, and m is an integer from 1 to about 10; and
(ii) an acid.
As used herein, the term hydrocarbyl chain means an alkyl or alkenyl chain.
Preferred amidoamine compounds are those corresponding to formula (I) in which
R1 is a hydrocarbyl residue having from about 11 to about 24 carbon atoms,
R2 and R3 are each independently hydrocarbyl residues, preferably alkyl groups, having from 1 to about 4 carbon atoms, and m is an integer from 1 to about 4.
Preferably, R2 and R3 are methyl or ethyl groups.
Preferably, m is 2 or 3, i.e. an ethylene or propylene group. Preferred amidoamines useful herein include stearamido-propyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyl- diethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethyl-amine, behenamidopropyldiethylmine, behenamidoethyldiethyl-amine, behenamidoethyldimethylamine, arachidamidopropyl- dimethylamine, arachidamidopropyldiethylamine, arachid-amidoethyldiethylamine, arachidamidoethyldimethylamine, and mixtures thereof.
Particularly preferred amidoamines useful herein are stearamidopropyldimethylamine, stearamidoethyldiethylamine, and mixtures thereof.
Commercially available amidoamines useful herein include: stearamidopropyldimethylamine with tradenames LEXAMINE S-13 available from Inolex (Philadelphia Pennsylvania, USA) and AMIDOAMINE MSP available from Nikko (Tokyo, Japan), stearamidoethyldiethylamine with a tradename AMIDOAMINE S available from Nikko, behenamidopropyldimethylamine with a tradename INCROMINE BB available from Croda (North Humberside, England), and various amidoamines with tradenames SCHERCODINE series available from Scher (Clifton New Jersey, USA).
Acid may be any organic or mineral acid which is capable of protonating the amidoamine in the conditioner composition. Suitable acids useful herein include hydrochloric acid, acetic acid, tartaric acid, fumaric acid, lactic acid, malic acid, succinic acid, and mixtures thereof. Preferably, the acid is selected from the group consisting of acetic acid, tartaric acid, hydrochloric acid, fumaric acid, lactic acid and mixtures thereof.
The primary role of the acid is to protonate the amidoamine in the hair treatment composition thus forming a tertiary amine salt (TAS) in situ in the hair treatment composition. The TAS in effect is a non-permanent quaternary ammonium or pseudo quaternary ammonium cationic surfactant.
Suitably, the acid is included in a sufficient amount to protonate more than 95 mole% (293 K) of the amidoamine present. In compositions of the invention, the level of linear cationic conditioning primary surfactant will generally range from 0.01 to 10%, more preferably 0.05 to 7.5%, most preferably 0.1 to 5% by total weight of the composition.
The linear fatty material
Figure imgf000010_0001
The composition of the invention comprises from 0.1 to 10 wt % of a linear fatty material.
The combined use of fatty materials and cationic surfactants in conditioning compositions is believed to be especially advantageous, because this leads to the formation of a structured lamellar or liquid crystal phase, in which the cationic surfactant is dispersed.
By "fatty material" is meant a fatty alcohol, an alkoxylated fatty alcohol, a fatty acid or a mixture thereof. Preferably the linear fatty material is selected from a fatty alcohol and a fatty acid, most preferably a fatty alcohol.
Preferably, the alkyl chain of the fatty material is fully saturated. Representative fatty materials comprise from 8 to 22 carbon atoms, more preferably 16 to 22.
Suitable fatty alcohols comprise from 8 to 22 carbon atoms, preferably 16 to 22, most preferably C16 to C18. Fatty alcohols are typically compounds containing straight chain alkyl groups. Preferably, the alkyl groups are saturated. Examples of preferred fatty alcohols include cetyl alcohol, stearyl alcohol and mixtures thereof. The use of these materials is also advantageous in that they contribute to the overall conditioning properties of compositions for use in the invention.
Alkoxylated, (e.g. ethoxylated or propoxylated) fatty alcohols having from about 12 to about 18 carbon atoms in the alkyl chain can be used in place of, or in addition to, the fatty alcohols themselves. Suitable examples include ethylene glycol cetyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (4) cetyl ether, and mixtures thereof.
The level of fatty material in conditioners of the invention is suitably from 0.01 to 10, preferably from 0.1 to 10, and more preferably from 0.1 to 5 percent by weight of the total composition. The weight ratio of cationic surfactant to fatty alcohol is suitably from 10:1 to 1 :10, preferably from 4:1 to 1 :8, optimally from 1:1 to 1 :7, for example 1:3. The particulate benefit agent (iii)
The composition of the invention comprises a particulate benefit agent. The particulate benefit agent is selected from conditioning actives, and mixtures thereof.
Preferably, the particulate benefit agent is a conditioning active selected from silicone emulsions, oils and mixtures thereof, most preferably silicone emulsions. More preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, hydrocarbon oils, fatty esters and mixtures thereof, most preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, polyisobutylene, cocoa butter, palm stearin, sunflower oil, soyabean oil, coconut oil and mixtures thereof.
The following silicones and oils are present in emulsified form in compositions of the invention.
Suitable oils are selected from hydrocarbon oils, fatty esters and mixtures thereof.
Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are branched chain hydrocarbon oils will preferably contain from about 12 to about 42 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers.
Specific examples of suitable hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof. Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used. Another suitable material is polyisobutylene.
Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols, Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically the mono-, di-, and tri-esters of glycerol and long chain carboxylic acids such as C1-C22 carboxylic acids. Preferred materials include cocoa butter, palm stearin, sunflower oil, soyabean oil and coconut oil.
Preferred silicones are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, more preferably selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of aminofunctionalised silicones with dimethicones.
Preferably, the particulate benefit agent is a conditioning active selected from silicone emulsions, oils and mixtures thereof, most preferably silicone emulsions. More preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, hydrocarbon oils, fatty esters and mixtures thereof, most preferably, the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, polyisobutylene, cocoa butter, palm stearin, sunflower oil, soyabean oil, coconut oil and mixtures thereof.
The following silicones and oils are present in emulsified form in compositions of the invention.
Suitable oils are selected from hydrocarbon oils, fatty esters and mixtures thereof.
Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are branched chain hydrocarbon oils will preferably contain from about 12 to about 42 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers.
Specific examples of suitable hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof. Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used. Another suitable material is polyisobutylene.
Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols, Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20. Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically the mono-, di-, and tri-esters of glycerol and long chain carboxylic acids such as C1-C22 carboxylic acids. Preferred materials include cocoa butter, palm stearin, sunflower oil, soyabean oil and coconut oil.
Preferred silicones are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, more preferably selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of aminofunctionalised silicones with dimethicones.
Preferred silicone emulsions do not comprise a hydrophobic modification, preferably the silicone emulsion is not a myristyloxyl modified silicone, most preferably not a myristyloxyl modified silicone or a cetyloxyl modified silicone. Most preferably, the silicone emulsions for use in the compositions of the invention are selected from emulsions of dimethicone, dimethiconol, amodimethicone and mixtures thereof.
Suitable silicones include polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable for use compositions of the invention are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Preferably, the silicone is selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of amino- functionalised silicones with dimethicones.
The viscosity of the emulsified silicone itself (not the emulsion or the final hair conditioning composition) is typically at least 10,000 cst at 25 °C the viscosity of the silicone itself is preferably at least 60,000 cst, most preferably at least 500,000 cst, ideally at least 1 ,000,000 cst. Preferably the viscosity does not exceed 109 cst for ease of formulation.
Emulsified silicones for use in the compositions of the invention will typically have a D90 silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 micron, ideally from 0.01 to 1 micron. Silicone emulsions having an average silicone droplet size (D50) of 0.15 micron are generally termed microemulsions.
Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.
Examples of suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions /microemulsions of dimethiconol. Cross-linked silicone gums are also available in a pre emulsified form, which is advantageous for ease of formulation.
A further preferred class of silicones for inclusion in compositions of the invention are amino functional silicones. By "amino functional silicone" is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group. Examples of suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone". A preferred amodimethicone is commercially available from Dow Corning as DC 7134.
Specific examples of amino functional silicones suitable for use in the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning).
Suitable quaternary silicone polymers are described in EP-A-0530 974. A preferred quaternary silicone polymer is K3474, ex Goldschmidt. Also suitable are emulsions of amino functional silicone oils with non ionic and/or cationic surfactant.
Pre-formed emulsions of amino functional silicone are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2-7224, DC2-8467, DC2-8177 and DC2-8154 (all ex Dow Corning).
Preferred conditioning actives are selected from the group consisting of polydimethylsiloxanes and aminofunctionalised silicones, blends of aminofunctionalised silicones with dimethicones, hydrocarbon oils, fatty esters and mixtures thereof.
The total amount of particulate benefit agent conditioning active is preferably from 0.1 wt % to 10 wt % of the total composition more preferably from 0.1 wt % to 5 wt %, most preferably 0.25 wt % to 3 wt % is a suitable level.
The linear cationic co-surfactant (iv)
The composition of the invention comprises a linear cationic co-surfactant, according to structure 2:
Figure imgf000015_0001
Structure 2 wherein:
• R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2 or a benzyl group;
• R3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 10 to 14; and
• X is an organic or inorganic anion; wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R3 in structure 2 by at least 3 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R3 in structure 2; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1:20 to 1:1 , preferably from 1:10 to 1 :1 , preferably 1:5 to 1 :2.
Preferably, the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R3 in structure 2 by from 3 to 12, more preferably from 4 to 12, even more preferably from 6 to 12, most preferably from 6 to 10 atoms, such that the carbon-carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R3 in structure 2.
R3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 3 to 14, more preferably 6 to 14, even more preferably 8 to 14, most preferably 10 to 14 .
The linear co-surfactant is present in an amount of from 0.01 to 5 wt %, preferably 0.1 to 2, more preferably 0.1 to 1.0, most preferably 0.2 to 0.7 wt % based on weight of total composition)
X is an organic or inorganic anion. Preferably, X comprises an anion selected from the halide ions; sulphates of the general formula RSO3 , wherein R is a saturated or unsaturated alkyl radical having 1 to 4 carbon atoms, and anionic radicals of organic acids.
Preferred halide ions are selected from fluoride, chloride, bromide and iodide. Preferred anionic radicals of organic acids are selected from maleate, fumarate, oxalate, tartrate, citrate, lactate and acetate. Preferred sulphates are methanesulphonate and ethanesulphonate.
Most preferably, X- comprises an anion selected from a halide, a methanesulfonate group and an ethanesulphonate group.
In a preferred embodiment, • R3 comprises linear alkyl chains, saturated or unsaturated, comprising an amido group and with atom-atom chain lengths of from 10 to 14;
• R2 comprises a proton or an alkyl chain having a carbon-carbon chain length of from Ci to C2; and
• X is selected from a halide, methanesulphonate and ethanesulphonate.
An example of a suitable material according to structure 2 is caprylamidopropyl dimethylamine, available from Sigma Aldrich.
Composition rheology
The compositions of the invention provide good viscosity and yield stress properties.
The compositions have a preferred yield stress range of from 30 to 200 Pascals (Pa), most preferably from 40 to 150 Pa peak value at 25 °C and 1 Hz. The method to measure the yield stress uses a serrated parallel-plate geometry, 40mm in diameter, attached to a suitable rheometer capable of applying oscillations at a constant frequency of 1Hz, and an amplitude sweep in the range of 0.1% to 2000%. The amplitude sweep range is applied at no more than ten points per decade of strain range covered at no more than 4 cycles per amplitude. The instrument should be operated under controlled strain, such as with the ARES G2 Rheometer from TA Instruments. The geometry’s temperature should be set at 25°C by means of, for example, a Peltier-controlled plate, or a recirculating bath. The yield stress is determined by plotting the elastic stress against strain amplitude, and at the peak of the curve, the maximum value is quoted as the yield stress. The elastic stress is calculated as the multiplication of (storage modulus)*(strain amplitude), each readily obtained from the instrument.
The compositions preferably have a viscosity of from 5,000 to 750,000 centipoise, preferably from 50,000 to 600,000 centipoise, more preferably from 50,000 to 450,000 as measured at 30°C on a Brookfield RVT using a Spindle A or B at 0.5 rpm for 60 seconds on a Helipath stand.
A preferred conditioner comprises a conditioning gel phase. These conditioners have little or no vesicle content. Such conditioners and methods for making them are described in WO2014/016354, WO2014/016353, WO2012/016352 and WO2014/016351. A composition comprising such a conditioning gel phase confers a Draw Mass of from 1 to 250 g, preferably 2 to 100 g, more preferably 2 to 50 g, even more preferably 5 to 40 g and most preferably 5 to 25 g to hair treated with the composition.
Draw Mass is the mass required to draw a hair switch through a comb or brush. Thus the more tangled the hair the greater the mass required to pull the switch through the comb or brush, and the greater the level of condition of the hair, the lower the Draw Mass.
The Draw Mass is the mass required to draw a hair switch, for example of weight 1 to 20 g, length 10 to 30 cm, and width 0.5 to 5 cm through a comb or brush, as measured by first placing the hair switch onto the comb or brush, such that from 5 to 20 cm of hair is left hanging at the glued end of the switch, and then adding weights to the hanging end until the switch falls through the comb or brush.
Preferably, the hair switch is of weight 1 to 20 g, more preferably 2 to 15 g, most preferably from 5 to10 g. Preferably, the hair switch has a length of from 10 to 40 cm, more preferably from 10 to 30 cm, and a width of from 0.5 to 5 cm, more preferably from 1.5 to 4 cm.
Most preferably, the Draw Mass is the mass required to draw a hair switch, for example of weight 10 g, length 20 cm, and width 3 cm through a comb or brush, as measured by first placing the hair switch onto the comb or brush, such that from 20 cm of hair is left hanging at the glued end of the switch, and then adding weights to the hanging end until the switch falls through the comb or brush.
Further Ingredients
The composition according to the invention may comprise any of a number of ingredients which are common to hair conditioning compositions.
Other ingredients may include, preservatives, colouring agents, polyols such as glycerine and polypropylene glycol, chelating agents such as EDTA, antioxidants such as vitamin E acetate, fragrances, antimicrobials and sunscreens. Each of these ingredients will be present in an amount effective to accomplish its purpose. Generally these optional ingredients are included individually at a level of up to about 5% by weight of the total composition. Preferably, the further ingredients include perfumes, preservatives, colours and conditioning silicones.
Mixtures of any of the above active ingredients may also be used.
Generally, such ingredients are included individually at a level of up to 2%, preferably up to 1 %, by weight of the total composition.
The compositions of the invention are preferably free from thickening agents for example thickening polymers. Examples of thickening polymers include polyquaternium thickeners (such as polyquaternium-10, polyquaternium-39); guar based thickeners (such as guar hydroxy ammonium chloride); Polyethylene Glycol (PEG) based thickeners (such as PEG 90M, PEG 14M, PEG 150 distearate), etc.
Embodiments of the invention are given in the following examples, in which all percentages are quoted by weight based on total weight unless otherwise stated.
Examples
Example 1: Composition 1 in accordance with the invention and Comparative
Composition A
Table 1: Compositions of Example 1 in accordance with the invention and a comparative Example A. Amounts are shown in wt % by wt of total composition.
Figure imgf000020_0001
Stearamidopropyl dimethylamine is available from Innolex, whilst Caprylamidopropyl dimethylamine is available from Sigma Aldrich.
The conditioners in examples 1 and A can be prepared using the following method:
1. Surfactants and fatty materials are added to a suitable vessel and heated to above the melting point of the fatty materials.
2. The molten blend is added to a suitable amount of water according to the compositions in Table 1, at a temperature of between room temperature and below the melting point of the fatty materials.
3. The mixture is mixed until opaque and thick.
4. The heat is then turned off, cooled to room temperature, and the rest of the water is added along with the remaining materials.
5. Finally, the formulation is mixed at high shear using a suitable homogenising device. Predicted conditioning performance (silicone deposition) is given in Table 2 below.
Figure imgf000021_0001

Claims

1. A conditioning composition comprising:
(i) 0.01 to 10 wt % of a linear cationic conditioning primary surfactant; selected from structure 1 and mixtures thereof:
R2 R
N Q _
R 2 X
1 © R2
Structure 1 wherein: o Ri comprises a linear alkyl chain having a carbon-carbon chain length of from Ci6 to C24, preferably C18 to C22; o R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2 or a benzyl group; and o X is an organic or inorganic anion;
(ii) 0.1 to 10 wt % of a linear fatty material;
(iii) a particulate benefit agent selected from conditioning actives and mixtures thereof; and
(iv) 0.01 to 5 wt % of a linear cationic co-surfactant, selected from structure 2 and mixtures thereof
Figure imgf000022_0001
Structure 2 wherein: o R2 comprises a proton or a linear alkyl chain having a carbon-carbon chain length of from Ci to C4, preferably Ci to C2or a benzyl group; o R3 comprises a linear alkyl chain comprising an amido group and having an atom-atom chain length of from 3 to 15, preferably 10 to 14; and o X is an organic or inorganic anion; wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom- atom chain length of R3 in structure 2 by at least 3 atoms, such that the atom-atom chain length of Ri in structure 1 is longer than the atom-atom chain length of R3 in structure 2; and wherein the molar ratio of linear cationic co-surfactant (iv) to linear cationic conditioning primary surfactant (i) is in the range of from 1:20 to 1 :1.
2. A conditioning composition as claimed in claim 1, wherein the carbon-carbon chain length of Ri in structure 1 differs from the atom-atom chain length of R3 in structure 2 by from 3 to 12, preferably from 6 to 10 atoms, such that the carbon- carbon chain length of Ri is structure 1 is longer than the atom-atom chain length of R3 in structure 2.
3. A conditioning composition as claimed in claim 1 or claim 2, wherein R3 comprises a linear alkyl chain having an atom-atomchain length of from 6 to 14, preferably 10 to 14.
4. A conditioning composition as claimed in any preceding claim, wherein the linear cationic conditioning primary surfactant is selected from behenyltrimethylammonium chloride, behentrimonium methosulphate, cetyltrimethylammonium chloride, and mixtures thereof.
5. A conditioning composition as claimed in any preceding claim, wherein the conditioning actives are selected from silicone emulsions and oils.
6. A composition as claimed in claim 5, wherein the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, hydrocarbon oils, fatty esters and mixtures thereof.
7. A composition as claimed in claim 6, wherein the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone, paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, polyisobutylene, cocoa butter, palm stearin, sunflower oil, soyabean oil, coconut oil and mixtures thereof.
8. A composition as claimed in claim 6 or claim 7, wherein the conditioning actives are selected from emulsions of dimethicone, dimethiconol, amodimethicone and mixtures thereof.
9. A conditioning composition as claimed in any preceding claim, wherein the particulate benefit agent conditioning active is present in an amount of from 0.1 wt % to 10 wt % of the total composition, more preferably from 0.1 wt % to 5 wt %, most preferably 0.25 wt % to 3 wt %.
10. A conditioning composition as claimed in any preceding claim, wherein the linear cationic co-surfactant is present in an amount of from 0.1 to 2 wt %, most preferably 0.2 to 0.7 wt %.
11. A conditioning composition as claimed in any preceding claim, wherein the molar ratios of linear cationic co-surfactants (iv) to linear cationic surfactants (i) are in the range of from 1:10 to 1:1, preferably 1:5 to 1:2.
12. A conditioning composition as claimed in any preceding claim, which has a viscosity of from 5,000 to 750,000 centipoise, as measured at 30°C on a Brookfield RVT using a Spindle A or B at 0.5 rpm for 60 seconds on a Helipath stand.
13. A conditioning composition as claimed in any preceding claim, wherein X- comprises an anion selected from a halide, a methanesulfonate group and an ethanesulphonate group.
14. A method of increasing deposition of a particulate benefit agent selected from conditioning actives, to hair comprising the steps of applying to hair a conditioning composition as defined in any of claims 1 to 13 and rinsing the hair with water.
PCT/EP2021/066150 2020-06-19 2021-06-15 Hair conditioning composition for improved deposition WO2021255047A1 (en)

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BR112022023902A BR112022023902A2 (en) 2020-06-19 2021-06-15 CONDITIONER COMPOSITION AND METHOD TO INCREASE THE DEPOSITION OF A PARTICULATE BENEFIT AGENT
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JP2005060271A (en) 2003-08-08 2005-03-10 Kao Corp Hair cosmetic
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US20050175569A1 (en) 2004-01-07 2005-08-11 Geraldine Fack Cosmetic compositions comprising a cation, a drawing polymer and a thickener, and cosmetic treatment processes
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WO2012016352A1 (en) 2010-08-03 2012-02-09 Shi Jianmin Humidification bottle and oxygen inhalator with humidification bottle
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0530974A1 (en) 1991-08-05 1993-03-10 Unilever Plc Hair care composition
WO2001043718A1 (en) 1999-12-17 2001-06-21 Unilever Plc Hair treatment composition containing two cationic surfactants
WO2002102334A2 (en) 2001-06-18 2002-12-27 Unilever Plc Hair treatment composition
JP2005060271A (en) 2003-08-08 2005-03-10 Kao Corp Hair cosmetic
US20050143268A1 (en) * 2003-11-14 2005-06-30 The Procter & Gamble Company Personal care composition containing a cleansing phase and a benefit phase
US20050175569A1 (en) 2004-01-07 2005-08-11 Geraldine Fack Cosmetic compositions comprising a cation, a drawing polymer and a thickener, and cosmetic treatment processes
WO2011134832A2 (en) * 2010-04-30 2011-11-03 Unilever Plc Composition
WO2012016352A1 (en) 2010-08-03 2012-02-09 Shi Jianmin Humidification bottle and oxygen inhalator with humidification bottle
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WO2019086311A1 (en) * 2017-10-30 2019-05-09 Unilever Plc Hair conditioning composition

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